Reacción #1253205

Ecuación de reacción

HI

n-BuLi

Compound 2

2,6-bis(t-Butyldimethylsilyloxy)anthraquinone

THF

Compound 1

1-Bromo-4-heptylbenzene

THF

→

light yellow brown solid

Rendimiento 51.0%

9,10-bis(4-Heptyl)phenyl-2,6-dihydroxyanthracene

Rendimiento 51.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato maintain the temperature below −60° C
2. 2
   workup.ADDITIONAfter addition
3. 3
   workup.ADDITIONadded dropwise to the above cooled solution
4. 4
   TemperaturaThe reaction was slowly warmed up to room temperature
5. 5
   workup.STIRRINGstirred at room temperature overnight
6. 6
   OtroThe deep brown reaction
7. 7
   Temperaturawas heated
8. 8
   Temperaturato reflux for 10 min. and most of the solvent
9. 9
   Otrowas removed under reduced pressure
10. 10
    ExtracciónThe reaction mixture was then extracted with methylene chloride three times
11. 11
    LavadoThe combined organic phase was washed with saturated sodium metabisulfate solution, water, and brine
12. 12
    Secadodried over MgSO4
13. 13
    OtroThe crude product was obtained as brown viscous oil
14. 14
    Otrowas purified by column chromatography on silica gel with 10/90 ether/hexane as an eluent

Procedimiento

Compound 2 (37 g, 0.079 mol) was dissolved in 200 mL of anhydrous THF and cooled to −78° C. To this solution was added n-BuLi (2.5 M in hexane, 94 mL, 0.24 mol) slowly to maintain the temperature below −60° C. After addition, the orange-yellow solution was stirred at −78° C. for an hour. Compound 1 (60.2 g, 0.24 mol) was dissolved in 100 mL of anhydrous THF and added dropwise to the above cooled solution. The reaction was slowly warmed up to room temperature and stirred at room temperature overnight. The reaction was quenched with HI aqueous solution (47% in water, 143 mL, 0.79 mol) and TBDMS group was also de-protected. The deep brown reaction was heated to reflux for 10 min. and most of the solvent was removed under reduced pressure. The reaction mixture was then extracted with methylene chloride three times. The combined organic phase was washed with saturated sodium metabisulfate solution, water, and brine, and dried over MgSO4. The crude product was obtained as brown viscous oil and was purified by column chromatography on silica gel with 10/90 ether/hexane as an eluent. The pure product was obtained as 22.4 g light yellow brown solid at 51% yield. 1H NMR (CDCl3) δ (ppm): 0.91 (t, J=7.0 Hz, 6H), 1.26-1.43 (m, 8H), 1.71-1.81 (m, 2H), 2.73 (t, J=7.8 Hz, 2H), 5.21 (s, br, 2H, OH), 6.89 (d, J=2.3 Hz, 2H), 6.96 (dd, J1=9.5 Hz, J2=2.5 Hz, 2H), 7.32 (d, J=8.6 Hz, 4H, phenyl), 7.35 (d, J=8.6 Hz, 4H, phenyl), 7.57 (d, J=9.4 Hz, 2H). 13C NMR (CDCl3): 14.16, 22.72, 29.26, 29.52, 31.60, 31.86, 35.90, 106.84, 118.58, 127.07, 128.46, 128.98, 129.64, 131.04, 134.94, 136.30, 142.10, 151.69. Mp 162-164° C. FD-MS: m/z 558 (M+).

Fuente